Solution Manual for A Microscale Approach to Organic Laboratory Techniques, 5th Edition

PART I: INTRODUCTION TO BASIC LABORATORY TECHNIQUES. Experiment

1: Introduction to Microscale Laboratory. Experiment

2: Solubility. Experiment

3: Crystallization. Experiment

4: Extraction. Experiment

5: A Separation and Purification Scheme. Experiment

6: Chromatography. Experiment

7: Simple and Fractional Distillation. Experiment

8: Infrared Spectroscopy and Boiling Point Determination. ESSAY: Aspirin. Experiment

9: Acetylsalicylic Acid. ESSAY: Analgesics. Experiment

10: Isolation of the Active Ingredient in an Analgesic Drug. Experiment

11: Acetaminophen. ESSAY: Identification of Drugs. Experiment

12: TLC Analysis of Analgesic Drugs. ESSAY: Caffeine. Experiment

13: Isolation of Caffeine. ESSAY: Esters — Flavors and Fragrances. Experiment

14: Isopentyl Acetate (Banana Oil). ESSAY: Terpenes and Phenylpropanoids. Experiment

15: Essential Oils: Extraction of Oil of Cloves by Steam Distillation. Essay: Stereochemical Theory of Odor. Experiment

16: Spearmint and Caraway Oil: (+)- and (-)- Carvones. Essay: The Chemistry of Vision. Experiment

17: Isolation of Chlorophyll and Carotenoid Pigments from Spinach. Essay: Ethanol and Fermentation Chemistry. Experiment 18 Ethanol from Sucrose. PART II: INTRODUCTION TO MOLECULAR MODELING. ESSAY: Molecular Modeling and Molecular Mechanics. Experiment

19: An Introduction to Molecular Modeling. ESSAY: Computational Chemistry — Ab initio and Semiempirical Methods. Experiment

20: Computational Chemistry. PART III: PROPERTIES AND REACTIONS OF ORGANIC COMPOUNDS. Experiment

21: Reactivities of Some Alkyl Halides. Experiment

22: Nucleophilic Substitution Reactions: Competing Nucleophiles. Experiment

23: Synthesis of n-Butyl Bromide and t-Pentyl Chloride. Experiment

24: 4-Methylcyclohexene. ESSAY: Fats and Oils. Experiment

25: Methyl Stearate from Methyl Oleate. ESSAY: Petroleum and Fossil Fuels. Experiment

26: Gas Chromatographic Analysis of Gasolines. ESSAY: Biofuels. Experiment

27: Biodiesel. ESSAY: Green Chemistry. Experiment

28: Chiral Reduction of Ethyl Acetoacetate; Optical Purity Determination Using a Chiral Shift Reagent. Experiment

29: Nitration of Aromatic Compounds Using a Recyclable Catalyst. Experiment

30: Resolution of (?????Phenylethylamine and Determination of Optical Purity. Experiment

31: An Oxidation-Reduction Scheme: Borneol, Camphor, Isoborneol. Experiment

32: Multi-Step Reaction Sequences: The Conversion of Benzaldehyde to Benzilic Acid. Experiment

33: Triphenylmethanol and Benzoic Acid. Experiment

34: Sonogashira Coupling of Iodosubstituted Aromatic Compounds with Alkynes Using a Palladium Catalyst. Experiment

35: Grubbs-Catalyzed Metathesis of Eugenol with 1,4-Butanediol to Prepare a Natural Product. Experiment

36: Aqueous-based Organozinc Reactions. Experiment

37: The Aldol Condensation Reaction: Preparation of Benzalacetophenones (Chalcones). Experiment

38: Preparation of an ???-Unsaturated Ketone via Michael and Aldol Condensation Reactions. Experiment

39: The Wittig Reaction: Preparation of 1,4-Diphenyl-1,3-butadiene. Experiment

40: Relative Reactivities of Several Aromatic Compounds. Experiment

41: Nitration of Methyl Benzoate. ESSAY: Local Anesthetics. Experiment

42: Benzocaine. Experiment

43: Methyl Salicylate (Oil of Wintergreen). ESSAY: Pheromones: Insect Attractants and Repellents. Experiment

44: N,N-Diethyl-m-toluamide: The Insect Repellent “OFF.” ESSAY: Sulfa Drugs. Experiment

45: Sulfa Drugs: Preparation of Sulfanilamide. Essay: Polymers and Plastics. Experiment

46: Preparation and Properties of Polymers: Polyester, Nylon, and Polystyrene. Essay: Diels-Alder Reactions and Insecticides. Experiment

47: The Diels-Alder Reaction of Cyclopentadiene with Maleic Anhydride. Experiment

48: Diels-Alder Reaction with Anthracene-9-methanol. Experiment

49: Photoreduction of Benzophenone and Rearrangement of Benzpinacol to Benzopinacolone. ESSAY:Fireflies and Photochemistry. Experiment

50: Luminol. ESSAY: The Chemistry of Sweeteners. Experiment

51: Analysis of a Diet Soft Drink by HPLC. PART IV: IDENTIFICATION OF ORGANIC SUBSTANCES. Experiment

52: Identification of Unknowns. PART V: PROJECT-BASED EXPERIMENTS. Experiment

53: Preparation of a C-4 or C-5 Acetate Ester. Experiment

54: Isolation of Essential Oils from Allspice, Cloves, Cumin, Caraway, Cinnamon, Fennel, or Star Anise. Experiment

55: Competing Nucleophiles in SN1 and SN2 Reactions: Investigations using 2-Pentanol and 3-Pentanol. Experiment

56: Friedel-Crafts Acylation. Experiment

57: The Analysis of Antihistamine Drugs by Gas Chromatography-Mass Spectrometry. Experiment

58: The Use of Organozinc Reagents in Synthesis: An Exercise in Synthesis and Structure Proof by Spectroscopy. Experiment

59: Synthesis of Naproxen by Palladium Catalysis. Experiment

60: The Aldehyde Enigma. Experiment

61: Synthesis of Substituted Chalcones: A Guided-Inquiry Experience. Experiment

62: Green Epoxidation of Chalcones. Experiment

63: Cyclopropanation of Chalcones. Experiment

64: Michael and Aldol Condensation Reactions. Experiment

65: Esterification Reactions of Vanillin: The Use of NMR to Solve a Structure Proof Problem. Experiment

66: An Oxidation Puzzle. PART VI: THE TECHNIQUES. Technique

1: Laboratory Safety. Technique

2: The Laboratory Notebook, Calculations, and Laboratory Records. Technique

3: Laboratory Glassware: Care and Cleaning. Technique

4: How to Find Data for Compounds: Handbooks and Catalogues. Technique

5: Measurement of Volume and Weight. Technique

6: Heating and Cooling Methods. Technique

7: Reaction Methods. Technique

8: Filtration. Technique

9: Physical Constants of Solids: The Melting Point. Technique

10: Solubility. Technique

11: Crystallization: Purification of Solids. Technique

12: Extractions, Separations, and Drying Agents. Technique

13: Physical Constants of Liquids: The Boiling Point and Density. Technique

14: Simple Distillation. Technique

15: Fractional Distillation, Azeotropes. Technique

16: Vacuum Distillation, Manometers. Technique

17: Sublimation. Technique

18: Steam Distillation. Technique

19: Column Chromatography. Technique

20: Thin-Layer Chromatography. Technique

21: High-Performance Liquid Chromatography (HPLC). Technique

22: Gas Chromatography. Technique

23: Polarimetry. Technique

24: Refractometry. Technique

25: Infrared Spectroscopy. Technique

26: Nuclear Magnetic Resonance Spectroscopy. Technique

27: Carbon-13 Nuclear Magnetic Resonance Spectroscopy Technique

28: Mass Spectrometry. Technique

29: Guide to the Chemical Literature. APPENDICES: Appendix

1: Tables of Unknowns and Derivatives. Appendix

2: Procedures for Preparing Derivatives. Appendix

3: Index of Spectra.